Triethylamine → HCID 86682348, compound

HRID 2281671Notes

Reaction equation

HRID 2281671 reaction equation
C(O)(=O)C(O)=O.[C:7]([O:11][C:12]([N:14]1[CH2:20][C:16]2([NH:19][CH2:18][CH2:17]2)[CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8].C(N(CC)CC)C.[F:28][C:29]1[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1>ClCCl>[F:28][C:29]1[CH:34]=[CH:33][C:32]([S:35]([N:19]2[C:16]3([CH2:15][N:14]([C:12]([O:11][C:7]([CH3:10])([CH3:8])[CH3:9])=[O:13])[CH2:20]3)[CH2:17][CH2:18]2)(=[O:37])=[O:36])=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 95884-Fluorobenzenesulfonyl chloride2×HCID 56962145tert-butyl 1,6-diazaspiro[3.3]heptane-6-carboxylate, hemioxalate salt

Product 1

HCID 86682348HCID 86682348, compoundYield 177.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 6-(tert-butoxycarbonyl)-1,6-diaza-spiro[3.3]heptane oxalate (350 mg, 719 μmol) in dichloromethane (6 mL) was added at 0° C. triethylamine (221 μl, 1.58 mmol) followed by 4-fluorobenzene-1-sulfonyl chloride (294 mg, 1.51 mmol). The reaction mixture was stirred at ambient temperature for 15 h. Further 4-fluorobenzene-1-sulfonyl chloride (100 mg, 0.51 mmol) and triethylamine (200 μl, 1.4 mmol) were added, the reaction mixture was stirred at ambient temperature for another 3 h. The reaction mixture was then diluted with dichloromethane 10 mL) and quenched with water (10 mL). The aqueous phase was extracted with CH2Cl2, and the combined organic phases were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by chromatography (SiO2; heptane:ethyl acetate 2:1) to give the title compound (456 mg, 89%) as a colorless oil. MS (EI) m/e: 357.1 (M+H)+.

Workup

  1. stirringthe reaction mixture was stirred at ambient temperature for another 3 h
  2. customquenched with water (10 mL)
  3. extractionThe aqueous phase was extracted with CH2Cl2
  4. washthe combined organic phases were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography (SiO2; heptane:ethyl acetate 2:1)

Sources & evidence

ORD record
ord-9c196789ee114bce966a9c460fa3730a
Source dataset
uspto-grants-2015_09
Patent number
US09139593B2

Reaction notes

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